TPGS-750-M: a second-generation amphiphile for metal-catalyzed cross-couplings in water at room temperature

J Org Chem. 2011 Jun 3;76(11):4379-91. doi: 10.1021/jo101974u. Epub 2011 May 9.


An environmentally benign surfactant (TPGS-750-M), a diester composed of racemic α-tocopherol, MPEG-750, and succinic acid, has been designed and readily prepared as an effective nanomicelle-forming species for general use in metal-catalyzed cross-coupling reactions in water. Several "name" reactions, including Heck, Suzuki-Miyaura, Sonogashira, and Negishi-like couplings, have been studied using this technology, as have aminations, C-H activations, and olefin metathesis reactions. Physical data in the form of DLS and cryo-TEM measurements suggest that particle size and shape are key elements in achieving high levels of conversion and, hence, good isolated yields of products. This new amphiphile will soon be commercially available.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Catalysis
  • Hydrophobic and Hydrophilic Interactions
  • Metals / chemistry*
  • Micelles
  • Polyethylene Glycols
  • Succinates / chemistry*
  • Sulfonamides / chemistry
  • Surface-Active Agents / chemistry
  • Temperature*
  • Thiadiazoles / chemistry
  • Vitamin E / analogs & derivatives*
  • Vitamin E / chemistry
  • Water / chemistry*


  • 2-(3-phenylpropionylamino)-1,3,4-thiadiazole-5-sulfonamide
  • Metals
  • Micelles
  • Succinates
  • Sulfonamides
  • Surface-Active Agents
  • Thiadiazoles
  • Water
  • Vitamin E
  • Polyethylene Glycols
  • tocophersolan